Uptown Vacations

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Where to stay in Uptown

Find the best Uptown areas and neighborhoods for the activities you enjoy most. Learn more about Uptown
Downtown Chicago showing a city

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotel + flight trips in Downtown Chicago

Uptown Hotel Deals

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$3,404 per night from May 29 to May 30
NT$3,404
per night
May 29 - May 30
7.6/10 Good! (2,578 reviews)
"Very clean"

Reviewed on 2024/5/14

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$4,818 per night from May 27 to May 28
NT$4,818
per night
May 27 - May 28
7.6/10 Good! (6,724 reviews)
"Great location for walking to both museums and Magnificent Mile. Restaurants on site if you don't get out to eat. Late check out (noon)."

Reviewed on 2024/5/14

Congress Plaza Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NT$6,775 per night from May 28 to May 29
NT$6,775
per night
May 28 - May 29
8.6/10 Excellent! (1,001 reviews)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"

Reviewed on 2024/5/10

The Westin Michigan Avenue Chicago
See all 4,207 properties in Uptown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does an Uptown vacation package cost?
From as little as , you can custom build your Uptown vacation package. Simply combine hotels, flights and rental cars and we’ll reward you with discounts.
How do I get a cheap travel package to Uptown?
Crafting your own Uptown vacation package with Expedia is a smart way to save. We have over 550 airlines and 1,000,000 hotel options across the globe. With such a broad range to select from, you’ll have no trouble pulling together your perfect escape.
Where should I stay in Uptown?
Cross Lincoln Park off your bucket list and then stay right around the corner. Experience the exciting atmosphere around this leading attraction and head there whenever the mood strikes!
What are the top hotels in Uptown?
When it comes to welcoming places to stay in Uptown, you can’t go past The Guesthouse Hotel. Be sure to browse our offers and land a great price.
How far in advance should I book my Uptown vacation?
While not all air carriers advertise ticket prices early, it’s usually possible to look up international airfares on Expedia up to 12 months in advance. This is the time when you’ll nab some fantastic bargains. If you’re purchasing tickets last minute, you might still get lucky. Sometimes the lowest prices emerge a few weeks before departure.
What does an Expedia Uptown travel package include?
Expedia has everything you need to lock in Uptown trip, but what goes into your package is entirely up to you. Pick from any combination of flights, rental cars and hotels. After some activities to keep you busy? Once you’ve made your booking, you can add them too. No matter your budget or style, there’s a deal to match your needs.
What should I know before booking an Uptown travel package?
We already have low prices. However, you’ll enjoy even better deals if you book your flights, hotels and car rentals together. With an Expedia package, you’ll get transparent pricing and lots of choice.
Can I choose my airline with an Uptown Expedia vacation package?
You sure can. Expedia has access to more than 550 airline partners around the world, so go with the carrier that’s a good fit for your budget needs.
If I'm not able to travel, can I cancel my Uptown vacation package?
It’s good to know that you can cancel your Uptown booking if your plans have changed. Whether you’ll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change for free if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Uptown

Image for Montrose Beach

Montrose Beach

Soak up the sun with views of Lincoln Park and Lake Michigan at this city beach known for its fun sports and extensive amenities.

Montrose Beach
Image for Lincoln Park

Lincoln Park

4.5/5(554 reviews)

This expansive public park along Lake Michigan offers museums, beaches, nature reserves and sporting facilities.

Lincoln Park
Image for Montrose Harbor

Montrose Harbor

With trails, a beach and a bird sanctuary, this spacious city harbor is a good place to sail from and a great place to hang out.

Montrose Harbor

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.